5-HT selective agents

Abstract

Substituted 8-alkoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroles; 5-alkoxy-2,3,4,4a,9,9a-hexahydro-1-H-indeno[2,1-c]pyridines; and 9-alkoxy-2,3,3a,4,5,9a-hexahydro-1H-benz[e]isoindoles are selective 5-HT receptor agents and are thus useful in the treatment of anxiety, depression, and hypertension.

We claim: 
     
       1. A compound of the formula ##STR19## wherein R 1  is hydrogen or an electron withdrawing group; R 2  is hydrogen, lower alkyl, or aralkyl;   m is an integer having a value of from 1 to 2 and n is 1;   R 4  is a member selected from the group consisting of hydrogen,   halogen,   lower alkyl,   lower alkoxy, and   aryl(lower alkyl);     or R 2  and R 4  taken together are --O--X--O-- where X is --CH 2  --, --CH 2  CH 2  -- or --CH 2  CH 2  CH 2  --;   R 3  is a group of the formula: ##STR20##  wherein q is an integer of from 0 to 3, R 8  and R 9  are hydrogen or lower alkyl, or R 8  and R 9  taken together form a ring of from 5 to 7 members and R 7  is divalent alkylene or alkenylene of from one to six carbon atoms; or a pharmaceutically acceptable salt thereof.     
     
     
       2. A compound as defined by claim 1 which is represented by the formula ##STR21## wherein R 1 , R 2 , and R 3  are as defined therein. 
     
     
       3. A compound as defined by claim 1 represented by the formula ##STR22## wherein R 1 , R 2 , and R 3  are as defined therein. 
     
     
       4. A compound as defined by claim 2 selected from the group consisting of 2-(3-(3,3-tetramethylene)glutarimidyl)propyl)-8-hydroxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole;   2-(3-(3,3-tetramethylene)glutarimidyl)propyl)-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)butyl-8-hydroxy-1,2,3,3a,8,8a-hexahydroindeno-[1.2-c]pyrrole;   2-(4-(3,3-dimethyl)glutarimidyl)butyl-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1.2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)butyl-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)butyl-5-chloro-8-hydroxy-1,2,3,3a,8,8a-hexahydroindeno[1.2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)butyl-5-chloro-8-methoxy-,2,3,3a,8,8a-hexahydroindeno[1.2-c]pyrrole;   2-(5-(3,3-tetramethylene)glutarimidyl)pentyl-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)cis-buten-2-yl-8-methoxy-1,2,3,3a,8,8a-hexahydro[1,2-c]pyrrole;   2-(4-(3,3-tetramethylene)glutarimidyl)trans-buten-2-yl-8-methoxy-1,2,3,3a,8,8a-hexahydro[1,2-c]pyrrole; or a pharmaceutically acceptable salt thereof.     
     
     
       5. A compound as defined by claim 3 selected from the group consisting of cis-2-(4-(3,3-tetramethylene)glutarimidyl)butyl-9-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benz[e]isoindole;   cis-2-(4-(3,3-tetramethylene)glutarimidyl)butyl-9-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benz[e]isoindole;   trans-2-(4-(3,3-tetramethylene)glutarimidyl)propyl-9-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benz[e]isoindole;   cis-2-(3-(3,3-tetramethylene)glutarimidyl)-propyl-9-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benz[e]isoindole; or a pharmaceutically acceptable salt thereof.     
     
     
       6. A method of treating hypertension in a mammal in need of such treatment comprising administering to such a mammal a therapeutically effective amount of a compound as defined by claim 1. 
     
     
       7. A pharmaceutical composition comprising a therapeutically effective amount of a compound as defined by claim 1 in combination with a pharmaceutically acceptable carrier.